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Cash and Investments - Net Gains (Losses) on Investments (Details)
$ in Millions, $ in Millions
12 Months Ended
Oct. 31, 2018
USD ($)
Oct. 31, 2018
CAD ($)
Aug. 03, 2018
USD ($)
Aug. 03, 2018
CAD ($)
Sep. 19, 2017
Sep. 06, 2017
Jul. 04, 2017
Dec. 31, 2018
USD ($)
Dec. 31, 2017
USD ($)
Dec. 31, 2016
Investment [Line Items]                    
Net gains (losses) on investments               $ 252.9 $ 1,467.5  
Share of profit (loss) of associates               221.1 200.5  
Proceeds from sales of interests in associates               444.8 $ 1,014.9  
Quess                    
Investment [Line Items]                    
Ownership percentage in equity method investment                 33.10% 42.10%
Proceeds from sales of interests in associates               $ 12.8    
EXCO Resources, Inc                    
Investment [Line Items]                    
Ownership percentage in equity method investment                 21.80% 15.80%
ICICI Lombard General Insurance Company Limited                    
Investment [Line Items]                    
Ownership percentage in equity method investment         9.90%     9.90%    
Grivalia                    
Investment [Line Items]                    
Ownership percentage in equity method investment           52.70% 52.60%      
Investments accounted for using equity method | Quess                    
Investment [Line Items]                    
Fair value of equity method investment               $ 1,109.5    
Share of profit (loss) of associates               889.9    
Investments accounted for using equity method | EXCO Resources, Inc                    
Investment [Line Items]                    
Share of profit (loss) of associates                 $ (121.6)  
Subsidiary and associates                    
Investment [Line Items]                    
Net realized gains (losses)               1,028.8 999.9  
Net change in unrealized gains (losses)               0.0 0.0  
Net gains (losses) on investments               1,028.8 999.9  
Other                    
Investment [Line Items]                    
Net realized gains (losses)               (0.1) 2.1  
Net change in unrealized gains (losses)               3.6 57.3  
Net gains (losses) on investments               3.5 59.4  
Common stocks | Investments accounted for using equity method | Grivalia                    
Investment [Line Items]                    
Share of profit (loss) of associates                 $ (51.3)  
Ownership percentage in equity method investment                 52.70%  
Bonds                    
Investment [Line Items]                    
Net realized gains (losses)               126.2 $ 445.7  
Net change in unrealized gains (losses)               (335.9) (167.7)  
Net gains (losses) on investments               (209.7) 278.0  
Preferred stocks                    
Investment [Line Items]                    
Net realized gains (losses)               (21.9) 0.2  
Net change in unrealized gains (losses)               (10.7) (0.5)  
Net gains (losses) on investments               (32.6) (0.3)  
Common stocks                    
Investment [Line Items]                    
Net realized gains (losses)               196.4 126.5  
Net change in unrealized gains (losses)               (581.1) 585.7  
Net gains (losses) on investments               (384.7) 712.2  
Debt and equity securities                    
Investment [Line Items]                    
Net realized gains (losses)               300.7 572.4  
Net change in unrealized gains (losses)               (927.7) 417.5  
Net gains (losses) on investments               (627.0) 989.9  
Derivatives and foreign currency net gains (losses)                    
Investment [Line Items]                    
Net realized gains (losses)               1,322.4 855.3  
Net change in unrealized gains (losses)               (1,069.5) 612.2  
Net gains (losses) on investments               252.9 1,467.5  
Derivatives:                    
Investment [Line Items]                    
Net realized gains (losses)               26.0 (624.0)  
Net change in unrealized gains (losses)               (46.6) 39.5  
Net gains (losses) on investments               (20.6) (584.5)  
Common stock and equity index short positions                    
Investment [Line Items]                    
Net realized gains (losses)               (46.8) (485.6)  
Net change in unrealized gains (losses)               8.6 67.7  
Net gains (losses) on investments               (38.2) (417.9)  
Common stock and equity index long positions                    
Investment [Line Items]                    
Net realized gains (losses)               (37.2) 21.6  
Net change in unrealized gains (losses)               (49.1) (2.0)  
Net gains (losses) on investments               (86.3) 19.6  
Equity warrant forward contracts                    
Investment [Line Items]                    
Net realized gains (losses)               75.4 0.0  
Net change in unrealized gains (losses)               38.5 0.0  
Net gains (losses) on investments               113.9 0.0  
Equity warrants and call options                    
Investment [Line Items]                    
Net realized gains (losses)               (15.1) 22.9  
Net change in unrealized gains (losses)               (54.8) 15.4  
Net gains (losses) on investments               (69.9) 38.3  
CPI-linked derivative contracts                    
Investment [Line Items]                    
Net realized gains (losses)               0.0 0.0  
Net change in unrealized gains (losses)               (6.7) (71.0)  
Net gains (losses) on investments               (6.7) (71.0)  
U.S. government bond forwards                    
Investment [Line Items]                    
Net realized gains (losses)               49.6 (174.5)  
Net change in unrealized gains (losses)               (2.9) 21.3  
Net gains (losses) on investments               46.7 (153.2)  
Other                    
Investment [Line Items]                    
Net realized gains (losses)               0.1 (8.4)  
Net change in unrealized gains (losses)               19.8 8.1  
Net gains (losses) on investments               19.9 (0.3)  
Foreign currency net gains (losses)                    
Investment [Line Items]                    
Net realized gains (losses)               (33.0) (95.1)  
Net change in unrealized gains (losses)               (98.8) 97.9  
Net gains (losses) on investments               (131.8) 2.8  
Investing activities                    
Investment [Line Items]                    
Net realized gains (losses)               (43.1) 0.8  
Net change in unrealized gains (losses)               (128.2) 88.0  
Net gains (losses) on investments               (171.3) 88.8  
Underwriting activities                    
Investment [Line Items]                    
Net realized gains (losses)               31.6 (74.9)  
Net change in unrealized gains (losses)               0.0 0.0  
Net gains (losses) on investments               31.6 (74.9)  
Foreign currency contracts                    
Investment [Line Items]                    
Net realized gains (losses)               (21.5) (21.0)  
Net change in unrealized gains (losses)               29.4 9.9  
Net gains (losses) on investments               $ 7.9 (11.1)  
Arbor Memorial Services Inc.                    
Investment [Line Items]                    
Net realized gains (losses) $ 111.8                  
Ownership percentage in equity method investment 43.40% 43.40%                
Proceeds from sales of interests in associates $ 179.2 $ 235.4                
Navacord Inc.                    
Investment [Line Items]                    
Net realized gains (losses)     $ 17.6 $ 22.7            
Proceeds from sales of interests in associates     $ 58.8 $ 76.3            
ICICI Lombard General Insurance Company Limited                    
Investment [Line Items]                    
Net realized gains (losses)                 $ 595.6  
Ownership percentage in equity method investment                 24.30%  
Proceeds from sales of interests in associates                 $ 908.5  
Unrealized gain on securities, reclassified to realized gain                 $ 334.5